US3141882A - Process for freparing free flowing - Google Patents
Process for freparing free flowing Download PDFInfo
- Publication number
- US3141882A US3141882A US3141882DA US3141882A US 3141882 A US3141882 A US 3141882A US 3141882D A US3141882D A US 3141882DA US 3141882 A US3141882 A US 3141882A
- Authority
- US
- United States
- Prior art keywords
- finely divided
- cyanuric chloride
- free flowing
- freparing
- caking
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- MCNLTUITFWBDSX-UHFFFAOYSA-N 4-chlorotriazin-5-amine Chemical class NC1=CN=NN=C1Cl MCNLTUITFWBDSX-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 239000000378 calcium silicate Substances 0.000 description 3
- 229910052918 calcium silicate Inorganic materials 0.000 description 3
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000004760 silicates Chemical class 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- 230000008029 eradication Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 229910052909 inorganic silicate Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/36—Only oxygen atoms having halogen atoms directly attached to ring nitrogen atoms
Definitions
- the present invention relates to an improved noncaking free fiowing finely divided cyanuric chloride composition, a process for its preparation and its use in the production of amino chlorotriazines.
- a finely divided cyanuric chloride by the addition of small quantities of a finely divided inorganic oxide or silicate.
- An especially suited oxide is a silicon dioxide produced by conversion of a volatile silicon compound with an oxidizing or hydrolyzing gas at elevated temperatures in the gas phase.
- gas phase silicas are available commercially as the wellknown trademarked products Aerosil and Cabosil. Similarly good results can be obtained with titanium dioxide or aluminum oxide produced in an analogous gas phase relation.
- finely divided silicic acid or silicates such as aluminum silicate or calcium silicate, produced by precipitation from aqueous solutions of alkali metal silicates are suitable to impart free flowing and non-caking characteristics to finely divided cyanuric chloride.
- the quantities of finely divided oxides or silicates required to render finely divided cyanuric chloride free flowing and non-caking is only about 0.3 to 3% by weight.
- the finely divided oxides or silicates can be added to the previously produced finely divided cyanuric chloride.
- the required quantity of the oxide or silicate can be injected into the gas stream with the aid of an inert gas preferably shortly before the cyanuric chloride is condensed or separated ofi.
- Amino chlorotriazines are useful as active substances for weed killers including such weed killers for selective eradication of weeds among cultivated plants as well as for total eradication or prevention of plant growth.
- weed killers including such weed killers for selective eradication of weeds among cultivated plants as well as for total eradication or prevention of plant growth.
- Example 1 Some kg. of cyanuric chloride are intimately mixed with 0.4% of Aerosil (finely divided silica). The caking cyanuric chloride is hereby transformed to a noncaking product.
- Aerosil finely divided silica
- Example 2 During the condensation of vaporized cyanuric chloride in the manufacture 1% of finely divided calcium silicate is continuously introduced by nitrogen in the vapor before injecting the vapor in the condensation chamber. The hereby obtained product is not caking.
- a method of producing a solid finely divided free flowing non-caking cyanuric chloride containing 0.3 to 3% of a finely divided inorganic substance selected from the group consisting of finely divided silicon dioxide, aluminum oxide, titanium oxide, silicic acid, calcium silicate and aluminum silicate intimately admixed therewith which comprises injecting the finely divided substance with the aid of an inert gas into a gas containing cyanuric chloride vapor distributed therein and condensing the cyanuric chloride vapor in contact with said injected finely divided substance to recover a solid free flowing non-caking cyanuric chloride containing 0.3 to 3% of the finely divided inorganic substance.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
3,141,882 PROCESS FOR PREPARTNG FREE FLOWHNG FENELY DiVTDED CYAN C CHLORIDE Tile Franz, Schwalbaeh, Taunus, Robert Richter, Heelikirchen, near Cologne, and Gerhard Bach, Wesseling,
Germany, assignors to Deutsche Goldund Silher- Scheideanstalt, Frankfurt am Main, Germany No Drawing. Filed Aug. 29, 1961, Ser. No. 134,571
Claims priority, application Germany Aug. 31, 1960 1 Claim. (Cl. 260-248) The present invention relates to an improved noncaking free fiowing finely divided cyanuric chloride composition, a process for its preparation and its use in the production of amino chlorotriazines.
it is known that solid finely divided cyanuric chloride easily cakes and therefore causes difficulties upon storage and during subsequent processing.
According to the invention, it was unexpectedly found that excellent free flowing properties and excellent processing characteristics can be imparted to finely divided cyanuric chloride by the addition of small quantities of a finely divided inorganic oxide or silicate. An especially suited oxide is a silicon dioxide produced by conversion of a volatile silicon compound with an oxidizing or hydrolyzing gas at elevated temperatures in the gas phase. Such gas phase silicas are available commercially as the wellknown trademarked products Aerosil and Cabosil. Similarly good results can be obtained with titanium dioxide or aluminum oxide produced in an analogous gas phase relation. Also finely divided silicic acid or silicates, such as aluminum silicate or calcium silicate, produced by precipitation from aqueous solutions of alkali metal silicates are suitable to impart free flowing and non-caking characteristics to finely divided cyanuric chloride. The quantities of finely divided oxides or silicates required to render finely divided cyanuric chloride free flowing and non-caking is only about 0.3 to 3% by weight.
The finely divided oxides or silicates can be added to the previously produced finely divided cyanuric chloride. On the other hand, when the cyanuric chloride is produced by trimerization of cyanogen chloride in the gas phase, the required quantity of the oxide or silicate can be injected into the gas stream with the aid of an inert gas preferably shortly before the cyanuric chloride is condensed or separated ofi.
It was furthermore found that the free flowing noncaking cyanuric chloride composition according to the invention could be used with excellent success for the production of amino chlorotriazines. Amino chlorotriazines are produced by reacting cyanuric chloride with Patented Juiy 21, 196
ammonia, primary or secondary amines in solvents, preferably in water. Amino chlorotriazines are useful as active substances for weed killers including such weed killers for selective eradication of weeds among cultivated plants as well as for total eradication or prevention of plant growth. Normally the caking characteristics of cyanuric chloride cause difliculties in the production of amino chlorotriazines therefrom. Often it was not possible to achieve a complete reaction with the result that the product had to be separated from unconverted cyanuric chloride. However, when the free flowing non-caking cyanuric compositions according to the invention are employed it is possible to carry out the reaction quantitatively.
Example 1 Some kg. of cyanuric chloride are intimately mixed with 0.4% of Aerosil (finely divided silica). The caking cyanuric chloride is hereby transformed to a noncaking product.
Example 2 During the condensation of vaporized cyanuric chloride in the manufacture 1% of finely divided calcium silicate is continuously introduced by nitrogen in the vapor before injecting the vapor in the condensation chamber. The hereby obtained product is not caking.
We claim:
A method of producing a solid finely divided free flowing non-caking cyanuric chloride containing 0.3 to 3% of a finely divided inorganic substance selected from the group consisting of finely divided silicon dioxide, aluminum oxide, titanium oxide, silicic acid, calcium silicate and aluminum silicate intimately admixed therewith which comprises injecting the finely divided substance with the aid of an inert gas into a gas containing cyanuric chloride vapor distributed therein and condensing the cyanuric chloride vapor in contact with said injected finely divided substance to recover a solid free flowing non-caking cyanuric chloride containing 0.3 to 3% of the finely divided inorganic substance.
Smolin et al.: s-Triazines and Derivatives, Intersciencc Pub. Inc., N.Y., 1959, page 55, QD 401 362.
Mullin: Crystallization, Butterworth and Co., 1961, page 184, QD 548 M7.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3141882A true US3141882A (en) | 1964-07-21 |
Family
ID=3456724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US3141882D Expired - Lifetime US3141882A (en) | Process for freparing free flowing |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3141882A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3290163A (en) * | 1963-10-30 | 1966-12-06 | Chas Elbreder & Company Inc | Free flowing treatment of glass beads |
| US3539565A (en) * | 1968-01-29 | 1970-11-10 | Geigy Chem Corp | Method for producing a solution of cyanuric chloride from gaseous cyanuric chloride |
| US4268408A (en) * | 1979-06-25 | 1981-05-19 | Ciba-Geigy Corporation | Solid cyanuric chloride handling improvements with tricalcium phosphate |
| EP0158362A1 (en) * | 1984-04-13 | 1985-10-16 | SKW Trostberg Aktiengesellschaft | Method for the production of solid cyanuric chloride |
| DE2839384C2 (en) * | 1978-09-11 | 1988-09-08 | Skw Trostberg Ag, 8223 Trostberg | Mixture containing cyanuric chloride for the synthesis of cyanuric acid derivatives and process for their preparation |
| WO1996006672A1 (en) * | 1994-08-26 | 1996-03-07 | Us Sulfamate, Inc. | Molten urea dehydrate derived compositions |
| US5716751A (en) * | 1996-04-01 | 1998-02-10 | Xerox Corporation | Toner particle comminution and surface treatment processes |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2882254A (en) * | 1953-12-11 | 1959-04-14 | Degussa | Preservation of the fluidity of polymethylmethacrylate by the addition of finely divied silica |
-
0
- US US3141882D patent/US3141882A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2882254A (en) * | 1953-12-11 | 1959-04-14 | Degussa | Preservation of the fluidity of polymethylmethacrylate by the addition of finely divied silica |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3290163A (en) * | 1963-10-30 | 1966-12-06 | Chas Elbreder & Company Inc | Free flowing treatment of glass beads |
| US3539565A (en) * | 1968-01-29 | 1970-11-10 | Geigy Chem Corp | Method for producing a solution of cyanuric chloride from gaseous cyanuric chloride |
| DE2839384C2 (en) * | 1978-09-11 | 1988-09-08 | Skw Trostberg Ag, 8223 Trostberg | Mixture containing cyanuric chloride for the synthesis of cyanuric acid derivatives and process for their preparation |
| US4268408A (en) * | 1979-06-25 | 1981-05-19 | Ciba-Geigy Corporation | Solid cyanuric chloride handling improvements with tricalcium phosphate |
| EP0158362A1 (en) * | 1984-04-13 | 1985-10-16 | SKW Trostberg Aktiengesellschaft | Method for the production of solid cyanuric chloride |
| US4591493A (en) * | 1984-04-13 | 1986-05-27 | Skw Trostberg Aktiengesellschaft | Process for obtaining solid cyanuric chloride |
| WO1996006672A1 (en) * | 1994-08-26 | 1996-03-07 | Us Sulfamate, Inc. | Molten urea dehydrate derived compositions |
| US5716751A (en) * | 1996-04-01 | 1998-02-10 | Xerox Corporation | Toner particle comminution and surface treatment processes |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3017348A (en) | Fire extinguishing compositions | |
| US3141882A (en) | Process for freparing free flowing | |
| US3375063A (en) | Ammonium polyphosphate preparation | |
| JPH0676233B2 (en) | Glass ampoule or tube bottle and method for manufacturing the same | |
| US2874027A (en) | Preparation of alkali metal phosphates | |
| US4120939A (en) | Hydrogen fluoride process | |
| Smyrl et al. | Hydroxide‐catalyzed synthesis of heterocyclic aromatic amine derivatives from nitriles | |
| US4255348A (en) | Preparation of dimethylaminosilanes | |
| US2544706A (en) | Phosphorus-and nitrogencontaining compounds | |
| US3555784A (en) | Separating ammonia from offgas obtained in the synthesis of melamine | |
| US2814635A (en) | Process of producing silicic acid esters | |
| US4008234A (en) | Process for the preparation of melon | |
| US3338673A (en) | Recovery of substantially anhydrous hydrogen fluoride from an impure aqueous ammonium fluoride solution | |
| KR100703547B1 (en) | Method for preparing melamine from urea | |
| US3308123A (en) | Method of separating melamine from waste gas | |
| US2988426A (en) | Method for producing polymeric phosphorus pentoxide | |
| US3223481A (en) | Production of orthophosphates | |
| JPS6236511B2 (en) | ||
| DE1134999B (en) | Manufacture of cyanuric chloride that does not stick together with good flowability | |
| AU731077B2 (en) | Crystalline melamine | |
| US3974262A (en) | Two stage process for producing ammonium phosphates | |
| US3974263A (en) | Process for producing ammonium phosphate in two stages | |
| US3690820A (en) | Production of ammonium nitrate | |
| US3274245A (en) | Recovery of acrylamide from its salt by vaporization with an inert gas | |
| US3321603A (en) | Recovery of urea from off-gases from the synthesis of melamine from urea in the gas phase which have been freed from melamine |